Sissification 101: Ch. 04

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"What a good idea! Both of those can be arranged," she approved, as she began slowly fucking my mouth. This cock was thicker than the others, and stretched my mouth a little more. But, like the cock sucker I was becoming, I was up for the challenge (although my clitty was still frustratedly flaccid inside its prison).

I focused on breathing through my nose, and just surrendering my face to be fucked, as Joan took charge.

After a couple minutes while she never roughly face fucked me, she pulled out and said, "Actually, I want you on your knees on the floor."

"The go to position for any sissy cock sucker," I said, almost every sissy video including dozens of clips of this submissive position.

"Exactly," she said, as she took my hand and guided me off the bed.

The dildo slipped partly out, but once I was on my knees, she shoved it all the way back in and at a slightly different angle, so it really teased my prostate.

"What in the world shall you do?" I joked, now on my knees, with a big dildo vibrating softly in my pussy.

I felt her cock touching my lips again, so I took it back into my mouth and began bobbing. I wanted to impress her. I wanted to look like such a sexy cock sucking slut.

"Oh yeah, you're a natural cock sucking slut," she moaned.

I moaned in response.

She pulled out and asked, "How badly do you want my cock?"

"I need it in my mouth so bad," I said, as she tapped my nose with it.

"What if Carter was here right now?" she asked.

"If you gave me permission, I'd suck his big black cock until he came down my throat, or all over my sissy face," I said, the declaration of a fantasy being realised someday making my caged clitty numb with desperation.

"And what if he wanted to fuck my cunt with his big black hammer?" Joan asked, as she slid the cock back in my mouth.

I bobbed for a few seconds, the idea so fucking hot, that when she pulled back out I blurted, "I'd watch you like the pathetic sissy cuckold I was born to be, and watch a real man satisfy my woman in ways I'll never be able to."

"And what if he comes in me?"

"Then I'd gobble down that cream pie as fast as I could," I answered, the idea of eating a mixture of her and his cum another hot twisted fantasy that drove me crazy.

"I see," she said, seeming a little further away.

Yet I felt her cock tap my lips.

I opened up and took the cock in my mouth, and was stunned!

This cock was flaccid.

This cock wasn't a fake strap-on.

This cock was real!

This cock had veins.

I could feel them pulsing.

I froze.

"Well, don't stop on my account, cock sucker," Carter ordered, his cockhead in my mouth... confirming all my sudden thoughts... Carter was actually here!

How did he get in here?

When did he get in here?

What had he heard? Seen?

I couldn't believe I had a real live black cock in my mouth. I did what any obedient sissy cock sucker would do, I took more of it into my mouth, as I marveled at the realization of such a long-held fantasy!

Joan said, her tone playful, "Have you figured out your surprise yet?"

I didn't answer with words, as I didn't want this big black cock to leave my mouth for even an instant, but I moaned as I felt it harden in my mouth. A feeling that was amazing to experience. A soft cock hardening in your mouth is so surreal, erotic and satisfying... knowing it's your mouth making it grow.

"Yeah, get it nice and hard, cock sucker," Carter instructed.

"Fuck, this is hot," Joan said, her tone conveying she was as turned on by watching me with a black cock in my mouth, as I was upon having said black cock in my mouth.

His cock was now completely hard, and stretching my mouth wide. I was in complete awe. I'd imagined being in this exact same position with a big black cock in my mouth hundreds, or even thousands of times. Yet nothing could have prepared me for the surreal tranquility and natural reality of experiencing the real thing.

I began bobbing slowly, trying to get used to a real cock in my mouth.

It felt so much warmer and fleshier (I know, a lame descriptor) than the plastic cock.

"You like watching your boyfriend suck my cock?" Carter asked, as I began bobbing a little faster.

"Yeah, it's so hot," Joan repeated. "Such a sexy cock sucker."

"Yeah, he's like all the other white cock suckers."

"How so?" Joan thankfully asking the question I wanted to ask.

"There are dozens of married men and college guys who come trooping into our secret glory hole bathroom," he said. "Well, actually not so secret recently."

"Really?" Joan asked. I was thinking the same thing, dying to hear more.

"Oh yeah, businessmen, coaches, professors, jocks, you name it," he said, as I bobbed, my clitty aching as I listened to this revelation. "All of them showing up to suck cock or get fucked... or both."

"Shit, that sounds so wild," Joan said.

"The odd couple shows up there too," he added. "Although most women just go to the frat house to get gangbanged by the boys."

"You had me at frat house," Joan joked.

"They'd love you," he said, as I imagined a dozen black men taking turns triple teaming my hot girlfriend.

"You're so sweet," she said, flirting.

I was taking a little bit more and more of his huge black cock. I only wished I could see it.

"Want to spit-roast him?" Carter asked, making my eyes go wild.

"Fuck, yeah," Joan said, as she ordered, "get on all fours, Erica."

Carter pulled his dick out as I replied, "Yes, Mistress," and did exactly as she ordered me.

"Enjoying that real cock?" Joan asked, as she moved behind me.

"It's amazing," I admitted.

"Want to see the BBC that's going to be pounding my pussy pretty soon?"

"God, yes," I said lustfully, as she pulled the vibrating dildo out of my ass.

Joan took the blindfold off and enthused, "Isn't it beautiful?"

"Deliciously perfect," I said, staring at ten inches of black cock right in front of my face.

"Well, get sucking slut," Joan ordered, as she slid her cock into my pussy.

"Oh yes," I moaned, as her dick filled me.

"Oh yeah, fuck his ass," Carter said, watching me get fucked.

"Sissies have cunts," Joan pointed out. "Including mine."

"Touché," he chuckled, as he offered me his cock.

I opened my mouth and began sucking, as a second fantasy came true in just a couple of minutes. First I had a BBC in my mouth, and now I was being spit-roasted!

At first it was awkward though... as I couldn't get into a rhythm of both sucking a cock and getting fucked simultaneously.

Joan was fucking me hard, making it difficult to suck effectively.

After a couple minutes of awkwardness, Carter said, "This can be better. Let the slut do all the work."

"How so?" Joan asked.

"Let him rock himself back and forth, first taking my cock, and then yours," Carter suggested. "All you and I need to do is remain in place."

"Oh, like a rocking horse."

"Exactly."

"Hear that, slut?" she asked, slapping my ass.

I moaned in response as she stopped fucking me.

"Ride me, slut," Joan ordered, slapping me again.

I moaned, as I began rocking back and forth slowly.

I sucked Carter's big black thick cock.

I bounced back onto Joan's not quite as big black cock.

It was so much smoother and more exhilarating, this way of... taking two cocks at once.

"That's much better," Joan said.

"The boys will love him," Carter said, which turned me on even more. I wanted to be a great cock sucker... for every BBC who would offer me the privilege of worshipping his cock.

"Erica will suck every cock you offer her," Joan said, again reading my mind.

"He's a natural cock sucking faggot," Carter added.

"Yeah, she was born to suck dick," Joan said before adding, "but only black dick."

Before I even knew it, as I rocked back and forth like a natural fuck slut, I was taking two-thirds of Carter's cock in my mouth, which meant my throat was getting some noticeable action. My clitty was numb but my body on fire, this being another of my most intense moments ever...

"Keep sucking," Carter moaned, which gave me another rush, as it meant I was pleasing him.

"Come all over his face," Joan said a moment later, as she pulled out of me.

Carter grabbed my head and began face fucking me, furiously pistoning in and out of my mouth.

"Spray my slut's face with your dominant black cum," Joan moaned, so turned on from watching me get face fucked.

"The slut can really take my dick," Carter groaned, as he slammed all ten inches into my mouth, thus bludgeoning my throat wide open, which made me seriously gag! "Spoke too soon," he laughed, pulling out, and then resuming fucking my face less aggressively.

"It'll take practice before she can easily take ten inches in her slut mouth," Joan appraised, and then added, "So I'll make sure she gets lots of practice."

"Oh, fuck," he grunted, as he pulled out and exploded a massive load all over my shocked face.

Cum shot directly into my left eye, before I could think to close it. Rope after rope splattered my face, surprising me with how warm it was... although I'd fantasized about taking a load all over my face many times, I'd never actually considered it might be warm.

"Keep me hard for your girlfriend," Carter ordered me before adding, "ready to get fucked, slut?"

It was weird to hear my beloved Mistress Joan being called a slut, or to hear her say, "God, yes, I want you to slam that big black cock in my white cunt, while my tiny-clitty-caged boyfriend watches."

"You'll never want his tiny dick again," Carter said, as I nursed on his cock, completely humiliated and therefore turned on by their ridicule... speaking about me disparagingly as if I wasn't there.

Joan added to the humiliation by saying, "I never have."

Carter laughed, "Harsh."

"He's a great pussy muncher though," Joan admitted.

"He'd better be," Carter said, as he pulled out. He looked down at me, his cum all over my face. "Want to watch me fuck your girlfriend?"

"Yeah," I answered.

"Give our Master a better fucking answer than that," Joan snapped, as I felt cum dripping off my chin.

"Yes Master, I intended no disrespect; I want to see you fuck my hot girlfriend with your big black cock, and give her the pleasure I never could," I answered.

"Much better," Joan said, as she pulled me up and said, pointing, "Go sit on that chair."

I wiped some cum from my left eye, which stung a bit, and put it in my mouth as a natural reaction, thus satisfying my afore-mentioned curiosity. Paradoxically, it had very little taste, although it instantly made me want some more. (And happily, there was lots more all over my face!)

As I looked at the chair in question, much to my surprise... apparently Joan was full of them... a different dildo was strapped to the chair, sitting completely erect. When did she even do that?

I walked over to the chair, straddled it like a dirty slut, and slowly lowered myself onto it, getting quite the thrill as they both watched me impale myself.

"Shit, what a faggot," Carter said, as he watched the cock disappear in my pussy.

"She's already advancing in her training at an accelerated pace," Joan said, as I kept taking more of the cock in my pussy... this angle quite different than any previous position.

Having them both watching me struggle with the largest phallus I'd attempted so far enhanced my humiliation, which, as always, added to my sexual exhilaration.

"Shit, she has precum oozing out of her clitty even while it's soft," Carter chuckled.

"It can't help but be soft because of the cage; but cage or not, she's constantly wet whenever we play," Joan said, as I moved my fingers to my cage, felt the stickiness, and wanting to wow these two, especially Carter, and show him how big a sissy I was, I scooped some cum off the outside of my cage and put it in my mouth.

"Shit," Carter chuckled, "she's the biggest sissy I've ever seen!"

"And she's been at it less than a week; she's just getting started," Joan bragged, sounding proud of my progress.

"She looks quite cute in her lingerie," Carter said.

"Yes, I thought bridal would be a good look for her tonight," Joan said, as I groaned loudly as I'd lost my balance, and suddenly I was sitting down completely on the tall dildo, a numbing pain reminding me that this act wasn't natural.

"It's a good start," Carter said, "but it's important for him or her to understand her place."

"I think she already does," Joan said.

"She's well on her way, but she has to understand she's at the utter bottom of the sexual hierarchy, and always will be," Carter said, as he looked at her, snapped his fingers, and Joan instantly dropped before him.

"She knows her place," Joan stood up for me, as she reached for his still completely hard cock, "as do I, Master."

"Does she really?" Carter asked, as Joan took his cock in her mouth and thus exited their conversation for a while. "You see Erica, you're lower than straight cocksuckers, as they still consider themselves real men; lower than gay men, as they at least are proud of who they are; and far below women, who are just as nature intended them to be unless they shackle themselves with boundaries; and you're not even in the same stratosphere as black men, who are the pinnacle of creation."

"I understand, sir," I replied, his ridicule humiliating, yet all of it true. At this point I wasn't even noticing I was slowly grinding on the dildo.

"Sir?" he questioned, as Joan bobbed on his cock.

"Sorry, Master," I corrected.

"And I own your girlfriend, too," he said.

"Yes, Master," I acknowledged. "Just as long as she agrees."

"And you'll be at my beck and call from now on too," he added, as he pulled out of my girlfriend.

"Yes, he will be," Joan spoke for me... as these were uncharted waters. We'd agreed to do everything together, so any exceptions to that rule were in her wheelhouse.

"Do you always speak for him?" Carter asked, as he pulled Joan up from her knees.

"Usually; and for anything we haven't already agreed upon, always. He's my sissy after all," Joan said, "and I have the final say in any usage of him."

Carter chuckled as he picked Joan up like she was a feather, and tossed her onto the bed, "I can work with that."

Joan clarified, even as she got on all fours so she was facing me, "You may only fuck me when she's with me, but you may train her mouth whenever you see fit, or maybe just want to drop a load. Then when I deem she's ready, the same will apply to her cunt."

"That sounds reasonable," Carter agreed, as he got on the bed and moved behind her.

Her location was hot, but a little frustrating.

Hot: I could see the expressions on her face: her trembling lips, her lustful eyes, as she got fucked.

Frustrating: since she was pretty much facing me, I couldn't watch his big black cock slamming into her perfect pink pussy.

Carter asked me, as I writhed on my dildo and watched helplessly, "Little girl, do you want me to fuck your girlfriend and give her the pleasure you never could?"

"I do, Master," I admitted sheepishly, mixed feelings coursing through me.

Yes, I wanted her to get fucked like she wanted and deserved.

Yes, I was stimulated by the idea of being cuckolded by a young black man.

Yes, my caged clitty was trying its best to become like the Hulk, and go from meek to strong.

Yes, I wanted to listen to the sounds of pleasure escaping Joan's lips.

Yet there was a growing insecure side, even though Joan had reassured me. What if Joan eventually found me obsolete and redundant? Fuck, even I couldn't think of any good reasons for her to keep me around when a ten-inch black dick was available to her.

"You do want what?" Joan demanded, clearly annoyed by my answer, as it seemed Carter was teasing her pussy with his dick, but not yet penetrating her. "Spit it out, sissy!"

"Yes, I want to watch you slam that big black dick into my white girlfriend, and give her the pleasure I'm helpless to provide with my tiny, pathetic, caged clitty," I answered, shame and simultaneous exaltation coursing through me like they often did... tainted glory exorcising shame, like it always did.

"Beg him to shove his dick in me," Joan ordered, moaning as she was being teased by Carter, being frustrated to the point of growing desperation by Carter... yet the entire time looking directly at me. Even given all the obvious taboo kink of this moment, as well as the demolition of the last strands of any sort of masculinity I still pretended to, this multi-faceted encounter felt strangely romantic.

I said, continually grinding a little on the dick in my pussy, "Please, Master Carter, fill my beautiful girl's pussy with all ten inches of your impressive black manhood."

"Manhood," he laughed.

"I just want to acknowledge the obviously difference between us," I explained. "Tiny pathetic Asian clitty versus huge majestic black cock."

"Sounds about right," he chuckled, before asking Joan, "Ready for my cock, slut?"

"Oh God yes, Master, show my tiny-clittied sissy what a real man can do to a woman," Joan replied with feeling, even as her eyes remained locked onto mine... her words continuing to demean me, which, of course, only enhanced my submissive persona and my excited clitty even more.

"PLEASE fill her up with that big black cock," I added, anxious to see her expression once he slid that massive hammer into her, making my clitty burn with desire.

"As you two sluts wish," he said, as he slid inside her assumedly soaked pussy.

I watched Joan's face as her eyes went big, and a loud moan of undeniable excitement burst from her lips.

"Oh yes, so fucking big," Joan said, still looking into my eyes.

"She's taking all ten inches pretty easily, sissy," Carter said, before adding, "like I expect you to be able to do pretty soon."

"Yes, Master," I distractedly agreed, only focused at the moment on the pleasure Joan was experiencing, even though I was obviously more than a little intrigued about what it would feel like when I was able to replace Joan.

"Oh yes, I can't wait to see you fuck her virgin pussy and tear it apart," Joan moaned.

Carter bucked his hips once while deep inside her. "Oh, she'll be walking bow-legged for a week."

"Mother fucker, yes, more, more," Joan begged; I'm not sure whether she was begging to hear more about his eventually tearing my pussy apart, or for more of getting her pussy pounded hard and rough right now... likely both.

Carter bucked his hips again and asked, "Think she'll be able to take this?"

"Oh yes, fuck," Joan moaned, "she'll take whatever I tell the slut to take."

Carter again bucked his hips deep into my hot girlfriend.

"Jesus fucking Christ," the not overly religious Joan bellowed.

"You're pretty fucking tight," Carter said, as he bucked a fourth time.

"I haven't had a real dick inside me for years," she admitted, still looking directly at me. Shame! Excitement!

"Well, we'd better make up for lost time," Carter said, as he moved both of his large manly hands to her hips and began fucking her.

They were definitely not making love.

They were definitely fucking.

"Oh God, yes, fuck me," Joan moaned loudly, as she was already feeling more pleasure than I'd ever given her back when I still had pretentions to having a penis. No way can anyone ever fake that level of rapture! Her cheeks were ruby red with stimulation. Her eyes were full of raw lust. Her hips were trembling. And her moans? Fuck, I could never make her sound like that.

I could also hear Carter's body slamming against hers as Joan took all ten inches inside her slim frame with lustful rapture.

"You like watching me getting royally fucked, sissy?" Joan asked, as I continued consciously grinding on the cock inside me, envious of the real big black cock Joan was taking... my clitty burning with desire.